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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 15:12:47 UTC

Update Date

2023-02-21 17:16:35 UTC

HMDB ID

HMDB0003290

Secondary Accession Numbers

HMDB03290

Metabolite Identification

Common Name

Gulonic acid

Description

Gulonic acid, also known as gulonate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Gulonic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make gulonic acid a potential biomarker for the consumption of these foods. Gulonic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Gulonic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900142D          

 13 12  0  0  1  0            999 V2000
   24.6507  -16.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9363  -18.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3652  -18.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2219  -16.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7940  -17.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7930  -17.4202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5074  -18.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6507  -17.4202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.9363  -17.8328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.3652  -17.8328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.2219  -17.4202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.0795  -17.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5074  -17.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  1  0  0  0
 10  3  1  1  0  0  0
 11  4  1  6  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003290

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5-/m1/s1

> <INCHI_KEY>
RGHNJXZEOKUKBD-KKQCNMDGSA-N

> <FORMULA>
C6H12O7

> <MOLECULAR_WEIGHT>
196.1553

> <EXACT_MASS>
196.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.160552515423085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

> <ALOGPS_LOGP>
-2.57

> <JCHEM_LOGP>
-3.4097443106666665

> <ALOGPS_LOGS>
-0.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.593710458724516

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.388205574321856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974220927705365

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
38.27100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gulonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      46.015 -30.978   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      44.681 -34.828   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.348 -34.828   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      43.348 -30.978   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      50.015 -33.288   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      40.680 -32.518   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      42.014 -34.828   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      46.015 -32.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.681 -33.288   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.348 -33.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.348 -32.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      48.682 -32.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.014 -33.288   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7   13                                                            
CONECT    8    1    9   10                                                  
CONECT    9    2    8   11                                                  
CONECT   10    3    8   12                                                  
CONECT   11    4    9   13                                                  
CONECT   12    5   10                                                       
CONECT   13    6    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gulonate	Generator
Gulonic acid, (L)-isomer	MeSH
Gulonic acid, ion (1-), (L)-isomer	MeSH
Gulonic acid, monosodium salt, (L)-isomer	MeSH
D-Gulonate	HMDB
D-Gulonic acid	HMDB
L-Gulonate	HMDB
L-Gulonic acid	HMDB

Chemical Formula

C₆H₁₂O₇

Average Molecular Weight

196.1553

Monoisotopic Molecular Weight

196.058302738

IUPAC Name

(2R,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

Traditional Name

gulonic acid

CAS Registry Number

20246-53-1

SMILES

OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O

InChI Identifier

InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5-/m1/s1

InChI Key

RGHNJXZEOKUKBD-KKQCNMDGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Monosaccharide
Fatty acyl
Fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0003290)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0003290)

Organ

Placenta (HMDB: HMDB0003290)

Source

Endogenous

Endogenous (HMDB: HMDB0003290)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Ascorbate Biosynthesis (PathBank: SMP0063817)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	159 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.4	ChemAxon
logS	-0.09	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.27 m³·mol⁻¹	ChemAxon
Polarizability	17.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.165	31661259
DarkChem	[M-H]-	136.808	31661259
DeepCCS	[M+H]+	149.135	30932474
DeepCCS	[M-H]-	146.767	30932474
DeepCCS	[M-2H]-	180.007	30932474
DeepCCS	[M+Na]+	155.048	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	147.3	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	134.1	32859911
AllCCS	[M+Na-2H]-	135.2	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gulonic acid	OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O	3328.4	Standard polar	33892256
Gulonic acid	OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O	1773.7	Standard non polar	33892256
Gulonic acid	OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O	1797.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gulonic acid,1TMS,isomer #1	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	1796.7	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #2	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	1788.4	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #3	C[Si](C)(C)O[C@H]([C@@H](O)[C@@H](O)C(=O)O)[C@H](O)CO	1752.9	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #4	C[Si](C)(C)O[C@H]([C@@H](O)[C@H](O)CO)[C@@H](O)C(=O)O	1757.3	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #5	C[Si](C)(C)O[C@@H](C(=O)O)[C@H](O)[C@@H](O)[C@H](O)CO	1754.6	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO	1778.3	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	1868.4	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #10	C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O)[C@H](O)CO	1819.9	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #11	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1830.8	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #12	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1835.9	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #13	C[Si](C)(C)O[C@@H](C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1826.5	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #14	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1825.1	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #15	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@H](O)CO	1823.3	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	1836.6	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #3	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1832.5	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #4	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1851.7	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1857.7	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #6	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	1849.6	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #7	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1840.6	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #8	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1849.4	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #9	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1850.8	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	1886.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #10	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1883.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #11	C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O)[C@@H](CO)O[Si](C)(C)C	1885.0	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #12	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1903.9	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #13	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1895.8	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #14	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1891.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #15	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1897.5	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #16	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1893.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #17	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1874.5	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #18	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1878.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #19	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1883.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1890.1	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #20	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1854.0	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #3	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1909.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #4	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1900.3	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1884.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #6	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1902.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #7	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1898.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #8	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1883.2	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #9	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1892.5	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1919.5	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #10	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1926.6	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #11	C[Si](C)(C)O[C@@H]([C@@H](CO)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1919.4	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #12	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1938.2	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #13	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1940.0	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #14	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1931.9	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #15	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1922.1	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #2	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1939.4	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #3	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1948.7	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #4	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1931.8	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #5	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1936.2	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #6	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1945.3	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #7	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1928.6	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #8	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1936.7	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #9	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1943.0	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1927.2	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #2	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1942.2	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #3	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1935.7	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #4	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1931.0	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1910.7	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1935.9	Semi standard non polar	33892256
Gulonic acid,6TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1983.7	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	2088.9	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	2075.2	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)[C@@H](O)C(=O)O)[C@H](O)CO	2032.4	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)[C@H](O)CO)[C@@H](O)C(=O)O	2021.7	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@H](O)[C@@H](O)[C@H](O)CO	2056.9	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO	2063.9	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	2316.2	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O)[C@H](O)CO	2267.6	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2303.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2304.4	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2284.7	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2293.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@H](O)CO	2298.2	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	2288.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2282.6	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2329.8	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2319.3	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	2311.2	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2291.1	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2325.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2319.9	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	2520.2	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2551.5	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2532.1	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2578.3	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2575.3	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2566.0	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2577.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2570.6	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #17	CC(C)(C)[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2534.1	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2550.2	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2555.9	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2532.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2526.3	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2578.0	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2559.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2521.4	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2586.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2568.6	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2562.1	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2563.4	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2766.5	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2773.7	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)O[C@@H]([C@@H](CO)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2798.7	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2799.5	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2790.9	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2786.9	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2762.0	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2821.6	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2802.6	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2810.2	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2802.1	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2793.9	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2803.2	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2798.2	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2792.2	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	3009.4	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	3005.2	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2991.5	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2988.2	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2988.3	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2997.1	Semi standard non polar	33892256
Gulonic acid,6TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3213.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Gulonic acid GC-MS (6 TMS)	splash10-067l-0897000000-a5adc23ee8062f1b4496	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Gulonic acid GC-MS (Non-derivatized)	splash10-067l-0897000000-a5adc23ee8062f1b4496	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gulonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tu-9500000000-abc0b019db16afd3352b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gulonic acid GC-MS (6 TMS) - 70eV, Positive	splash10-03fr-6121297000-698854fa2453487a1d69	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gulonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gulonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gulonic acid GC-MS (TBDMS_6_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gulonic acid GC-MS ("Gulonic acid,6TBDMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gulonic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0002-0900000000-51cc4bff4f073ec29dc7	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gulonic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-06yk-9200000000-36fd28057c23b3aeb698	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gulonic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-01t9-9200000000-14a6bd042df22e1334ec	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 10V, Positive-QTOF	splash10-004j-2900000000-9081b4da0decbd05f2d0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 20V, Positive-QTOF	splash10-03di-9400000000-79c4dcd310d5cacca35c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 40V, Positive-QTOF	splash10-08i9-9000000000-62e401fc518adf3537bd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 10V, Negative-QTOF	splash10-0adu-9600000000-2d2f2523012a7bbe0e8a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 20V, Negative-QTOF	splash10-0a4u-9300000000-00e22f3157480a68e695	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-87d75121bafb2a63a0f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 10V, Negative-QTOF	splash10-004i-9100000000-ff1473e44b436e4f8fa5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 20V, Negative-QTOF	splash10-0a6r-9000000000-aac8778b161b37e56a13	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 40V, Negative-QTOF	splash10-0a6r-9000000000-8920759ff7b62f308018	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 10V, Positive-QTOF	splash10-024m-8900000000-7ecf18d54cb462c04558	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 20V, Positive-QTOF	splash10-074i-9000000000-a24dd2cb9b57deddeaae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gulonic acid 40V, Positive-QTOF	splash10-08fr-9000000000-ae48df53c8de11d2cae6	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Endoplasmic reticulum

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

344

PubChem Compound

152304

PDB ID

Not Available

ChEBI ID

87753

Food Biomarker Ontology

Not Available

VMH ID

GULN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

ASHWELL G, KANFER J, SMILEY JD, BURNS JJ: Metabolism of ascorbic acid and related uronic acids, aldonic acids, and pentoses. Ann N Y Acad Sci. 1961 Apr 21;92:105-14. [PubMed:13684759 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Regucalcin

General function:: Involved in calcium ion binding
Specific function:: Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:: RGN
Uniprot ID:: Q15493
Molecular weight:: 33252.53

Reactions

L-Gulonolactone + Water → Gulonic acid	details

Enzyme Details

2. Lambda-crystallin homolog

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: CRYL1
Uniprot ID:: Q9Y2S2
Molecular weight:: 35418.91

Reactions

Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADH	details
Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADH + Hydrogen Ion	details

Showing metabocard for Gulonic acid (HMDB0003290)

MOL for HMDB0003290 (Gulonic acid)

3D MOL for HMDB0003290 (Gulonic acid)

3D SDF for HMDB0003290 (Gulonic acid)

3D-SDF for HMDB0003290 (Gulonic acid)

PDB for HMDB0003290 (Gulonic acid)

3D PDB for HMDB0003290 (Gulonic acid)

SMILES for HMDB0003290 (Gulonic acid)

INCHI for HMDB0003290 (Gulonic acid)

Structure for HMDB0003290 (Gulonic acid)

3D Structure for HMDB0003290 (Gulonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions